


Babysitter to the Max

by Moonstone_Plus



Category: Sydney to the Max (TV)
Genre: Gay Sex, M/M, Masturbation, Sleep Sex, Smut
Language: English
Status: In-Progress
Published: 2020-09-05
Updated: 2020-09-05
Packaged: 2021-03-06 21:54:51
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 5,169
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26296018
Author URL: https://archiveofourown.org/users/Moonstone_Plus/pseuds/Moonstone_Plus
Summary: Max Reynolds has a new babysitter and for the first time in his life, it isn't some old lady planning on ruining his fun. With the night quickly becoming everything that young Max ever wanted from a babysitter.
Kudos: 7





	Babysitter to the Max

Thirteen-year-old Max Reynolds was currently making a mad dash around his house, jumping down stairs and going in one door and out the other. He was a rainbow blur in that silly colourful jacket, racing around trying to find his kneepads and clip-on nose ring so he would look cool for the Dog Boys. Every now and then he would trip over something, or ram into an object hard enough to have the wind knocked from his guts. But nothing stopped Max for long.

Not even his mother, who was constantly spinning around trying to talk to her son whenever he would rush past. 

It was early Saturday morning and the sun was shining brightly into their home, condensation fading from the windows to reveal a bright world outside that Max was eager to run out into for a day of fun. 

However, that bright and bubbly excitement was instantly stolen away from the thirteen-year-old when he finally had all of his skating gear. Kneepads strapped on tightly and the annoying helmet he would be ditching into a bush out front the moment he got outside was on his head. A black board with rich detailing on the bottom - A present from his father last christmas - was tucked under Max’s arm and there was a broad smile from ear-to-ear on his face. Flickering just for a moment upon reaching the front door. Which happened to have his mother, Judy, barring the way. Her arms were crossed, Judy wore a firm expression that screamed how little chance there would be to change her mind on whatever this was about.

Max gulped and backed down a step, his brown eyes looking up at his mother.

“Umm… g-good morning?” He mumbled, seeing no change in her expression. “Can I get to the door, mom?”

“No.” Judy extended a hand, reaching out for the board. Much to her annoyance, Max clapped her hand hoping that it was a low five. “The board, young man. You aren’t going skating today; remember I have to leave, and you have a babysitter coming in ten minutes?”

Max released a loud groan, slouching low. “Ughhh, mom! I’m thirteen, I don’t need a babysitter!”

“Really?” Shifting weight to one leg, Judy gave him a skeptic look. “And how do you expect to care for yourself all night? Can you make your own dinner? Can you lock up the house? Can you keep yourself safe? Can I trust you not to make my house a mess?”

With each new question being thrown in his face, the young boy’s back arched lower and he became more irritated. That beautiful day outside looked better than it had when he woke up; A nice warm breeze would be blowing through right now and instead of feeling it whipping past he was standing there with a mother blocking the exit. 

Seeing himself as a ‘big boy’ capable of standing up for himself, and throwing a party without his mother finding out, Max crossed his arms and puffed out his chest. He stood on his tiptoes to seem taller. “If you just gave me money for pizza, I won’t have to make dinner! And I mean, come on! I can take care of myself!” 

“You still sleep with a teddybear, Max!” Judy rolled her eyes before checking her watch. “Sh-! I have to go. No leaving this house. The babysitter will be here soon, they know the rules. And no skating!” 

Judy was out the door a moment later, heading off for some business or school thing Max never bothered listening to her explaining. 

Max waited for her to finally be gone before making his move; Rushing back to the bedroom he threw open the window and squeezed out and onto the tree, nimbly standing on its strong branch to carefully make his way down to the soft grass below. That was, he would have started the long climb down its truck had his mother not been standing there with a very unsurprised look on her face.

“I… I’m just going to go back in here now,” The boy said. He pointed to the window and started back to his bedroom.

Nodding along, his mother looked disapproving. “Yes. Yes, you will young man.” 

Later, slouching low on the living room couch, face propped up on his fists, Max wore a sour expression. Eyes on the clock, watching it tick over for about seven minutes. Even after the car pulled out of the driveway it was best to wait out Judy. Only this time waiting wouldn’t work either. The babysitter would be there any second to put an end to any and all plans of getting out of the house or getting to enjoy it alone.

All week he waited for his mother to get out of the house, leading to a night alone where he could invite over the Dog Boys, skate whenever and for however long he liked. Of course she had to go and ruin it with some babysitter that probably never took care of a kid in her life.

So it was a surprise when Max opened the door to some nineteen-year-old dirty-blond skater boy wearing a friendly grin and baggy clothes. On instinct the young boy almost slammed the door shut, but held back. Though he did keep a tight grip on the door. The skater boy shifted his weight and offered a little ‘hey man’ that fell upon deaf ears. Max was too surprised to listen. Entranced by a deep-set pair of blue eyes that had a small twinkle in them staring down at Max, who was agape wondering if his mother hired the wrong babysitter. 

Sensing the confusion, they offered a hand. “Hey man? I’m Colin, your mom hired me. Max, right?”

Max nodded.

“Cool, got the right place! I went next door by mistake… that Lady didn’t want me to leave…” The older boy smiled. His face was warm and made Max want to just giggle.

Sticking to his ‘cool dude’ attitude, Max hesitantly stepped aside to allow Colin inside. Colin entered happily, looking around at the house with an impressed look in his blue eyes, setting down a backpack next to the coffee table. Still not entirely convinced that this boy was supposed to take care of him for the night, Max’s eyes roamed all over Colin just to see if there was anything off about him but finding nothing. Why some high school age guy was babysitting was beyond the thirteen-year-old, but if Colin was cool as he looked then this could be an upside. 

Closing the front door, Max turned on his heel. Giving Colin a skeptic look, he crossed the room and dropped down on the couch without taking his eyes away. 

“So your mom gave me this list of rules for tonight, and it’s a pretty long one. Uh,” The blond looked through the list with an eyebrow raised. Rule after rule, everything on the sheet of paper detailed something that would suck the fun out of a casual boys night. When he reached the end Colin wondered if an old nun wrote it. “Woah how strict is she! No sugar, no drinking soda… no TV until after homework? That’s whack! Does your mom seriously expect people to follow this stuff, man?”

Max lowered his eyes. “It’s no fair, right?”

“No way,” Colin scrunched up the list and stuffed it into his pocket much to Max’s amazement. “How’s this: I make up some rules, and you don’t tell your mom?”

“Really?” Max exclaimed, jumping up from the couch. “That’s fu-”

Instantly Colin shot out a finger to the boy’s lips, a look of surprise in his eyes. “Ah, ah! First rule, no cursing.”

With the rule list gone out of both boy’s minds, Max returned to the couch and turned on the TV. The Dukes of Hazzard was on, entrancing the young boy who lost any focus on his new babysitter’s presence. 

Colin was kneeling, hunched over his bad and rifling through for something. When he started muttering something about how much he packed, the thirteen-year-old peeked over out of curiosity. There were more clothes in there Max noticed, looking over his shoulder, and a few little things he could not quite make out. A bandana fell out but got tucked away without a word. Some things ruffled around inside, getting louder when Colin’s hand closed around something and pulled it out in one swift motion. 

A bag of potato chips of all things.

“Hungry?” He offered, shaking the bad.

“Oh, um s-sure…” Confused why Colin brought potato chips when there was a bag or two in the pantry, Max dug in and took a handful. 

Colin joined him on the couch, bringing with him such a casual demeanor that Max could feel himself becoming more comfortable and sinking down and relaxing without either of them saying a word. In the corner of his eye, he looked Colin up and down. He was a handsome boy with messy hair brushed to one side and a little stubble on his chin but otherwise smooth-faced. A beautiful smile and laugh that made him seem a few years younger. That relaxing aura he brought into the house was such a welcome change to his mother’s strictness that Max actually found himself staring more at the older boy that at the TV. It was only a rerun, he argued in his mind to justify the need to stare at another boy.

He noticed that Colin squeezed himself into the couch corner, propping one foot up on his mother’s coffee table and slinging an arm over the couch. Pulling off cool and casual in a way that max could only wish to pull. He made a little attempt to copy, but his foot slipped from the wood and he ended up just looking awkward.

Looking over, Colin realised he hadn’t really gotten to know this kid at all. 

“So Max?” His voice was deep and husky, but with a hint of teenage pitch. “What kinda stuff are you into, man? I saw a skateboard when I came in; you like to skate or what?”

“I love it! B-but my mom never lets me… she thinks it’s too dangerous, and I can’t find anyone to teach me tricks,” Tapping his feet and staring at the TV, Max’s eyes flickered to Colin’s handsome face. Still with no idea why he was looking at him. “Um… what about you? I thought you would be a girl,”

Colin snickered and gave a little nod. “Yeaaah it’s actually my sister who is supposed to be babysitting. She had you booked but got sick. Soooo, you get me!”

Confused at first that Colin had dodged his question about interested, Max opened his mouth. Just as the first sound left him, Colin got to his feet and crossed the living room to grab his board. With the older boy admiring the detail and custom red wheels, the fourteen-year-old blushed. Just like with the Dog Boys, he was expecting to hear some grunt of approval or see Colin rolling his eyes and call it lame. But the older boy turned to him with an eager look in his eyes.

“Wanna skate, little dude? I’ll teach you, dude! Been skating since I was nine,” 

The happiness in the younger boy’s voice as he responded positively, thrilled that for the first time that a babysitter was actually going to skate with him. A happiness that only grew as he bolted for his bedroom to grab his good board, the one he used in his attempts to show off to the dog boys, before heading back downstairs. With a quickness that had Colin chuckling. As expected of someone dressed like that and so energetic to just get out in the big open world, the boy had no protection on him so before they left Max was forced into gear.

Max hated to feel like a dork but still felt cool being with Colin.

It had been one of the best times of his young life, with Jackson and Colin skating alone for a while before the park had been overrun by Jackson’s idols the Dog Boys and their leader Ricolli. While he found himself wanting to see Colin and Ricolli skate against each other, he didn’t want to ruin his chances with either. So he pushed for Colin to take him home, the boy working every excuse he had to get his hunky babysitter away from the hunky leader of the Dog Boys.

Colin had been hesitant to agree, but in the end had the thirteen-year-old on his back with two legs wrapped tightly around his waist. Max was kind of heavy, but since he had memories of doing this to his own babysitters Eddie and Ritchie back in the day, he couldn’t protest.

The sun was getting low by the time they reached home, the dim orange light shining on the two figures as they played for a few minutes in the yard; One refused to climb down and even attempted reaching up to climb onto the roof as an escape plan. It was only when the first street lamp buzzed to life that they had to huddle inside, throwing down their gear and sinking down onto the cough with tired sighs. In unison, the two boys yawned loudly. They had spent hours down at the skate park and getting lunch at a little hotdog stand close by. Neither felt hungry enough for dinner, so allowed themselves to cuddle into the couch.

Max nodded off first while Colin watched a movie through hazy, tired eyes.

He felt a blanket being placed over his body, so shifted over to cuddle up to the nineteen-year-old.

“Ohh, hey there…” Colin said softly, resting an arm on the sleeping boy. He didn’t last much longer before darkness fell over his vision and dreams invaded his mind, leaving the boys in late afternoon dimness. 

For an hour neither stirred or moved, snoring peacefully until Max abruptly entered a semi-lucid dream about his two idols: Colin and Riccoli were completely naked and making out, their hands roaming all over and exploring. Colin’s hands slipped down for a handful of Riccoli’s soft ass, squeezing the skater boy’s perky cheeks while their tongues were battling for dominance. As badly as Max yearned to see what the older boys were packing, he couldn’t quite imagine their cocks so the dream kept their bodies pinned tightly together.

That dream had been what woke him up, with wide eyes and a little sweat. Max shoved off the blanket, suddenly too hot for its warmth. The boy looked down to his shorts, finding himself supporting a small bulge. The outline of his cock brought a blush to his cheeks, but the boy reached down to curl his fingers around it and gave a little squeeze. 

“Oh man…” His voice was soft, trying not to wake the older boy. 

Turning slightly to look at Colin, he saw that the older boy was so deep in sleep that the moan did nothing but fall upon deaf ears.

Through the semi-darkness, Max looked up at the older boy with a look of intrigue, his brown eyes exploring Colin’s handsome face while deep in sleep. Even like that, Colin was easily one of the best looking guys he had met. Dirty-blond hair styled perfectly yet still looked messy, a strong jaw and, from what he saw whenever his tee rode up, a killer muscular body hidden underneath. Which, when Max thought about it, brought a blush to his face.

When he saw Colin’s abs earlier in the day, he hadn’t realised just how badly he wanted to see them again.

So, with his babysitter asleep, Max raised his head off of Colin’s leg and adjusted so he was on his knees. Both hands were gripping them hem of his babysitter’s shirt, slowly and carefully peeled the fabric up so he was able to once again see that stunning six-pack. 

Max took a sharp breath. 

Colin’s abs were godly, like they had been cut from stone. As the man took slow breaths his muscles flexed, showing off the amazing definition and how sexy his body really was. Max could only see half the six-pack, but was still taken aback by Colin’s body. Nothing like his own smoothness. 

“Oh man, he’s so…” His mind refused to say hot, but the word was there. 

Using a very light touch, the boy reached down and ran a finger along Colin’s deep V-line, following from the hem of his jeans and up the man’s side. Colin didn’t stir, so Max proceeded to gently feel up his abs, getting his first ever feel of muscles and loving it. Every touch made him want to remove Colin’s shirt and get the full view: Biceps, nipples, pecs, everything he could get his cheeky hands on.

However, without realising where he put it, Max’s hand was supporting him from a rather sensitive spot. Only when looking down did he notice what he was just touching.

“Oh my God!” He fell back and wiped his hand on the couch like it was somehow infected. “Ew, ew, ew, ew, ew! Ugh, I touched a dick! S-so… gross,”

After letting himself a moment to actually calm down, Max realised his hand felt no different. He felt no different. Acting on impulse, convincing himself that touching another boy wasn’t all that bad if it was just for curiosity. And after all, he had never seen another boy’s cock, having no idea how big they could get or anything. All of this lead to Max crawling slowly back onto the couch and readjusting Colin’s shirt so he could see the dirty-blond’s abs again. Although now he realised that leading up to Colin’s belly button was a thick trail of hair that came from his jeans. 

Following the treasure trail with a finger, Max reached Colin’s pants.

Now was his moment to choose. They were baggy enough that he could easily pull them down and get a look at an older boy’s dick, see its size and how much hair they got. 

“Fuck…” Max muttered. This felt so gay and yet the boy didn’t care enough to let it stop him. 

With a mind of its own the young boy’s hand started moving down to his own shorts, gripping around the hem. Max’s breathing was slow as he pulled down the shorts to just below his small sack, allowing them to cup his balls through a pair of tighty whities. Max’s four and a half inch cock was only semi-hard, still forming only a small bump in his underwear. Meanwhile his perky butt was still covered up. 

Massaging the bump, the boy’s moans were soft. Quiet so that Colin would not stir to find him in such a state, entranced by a lust he had never felt before. He wanted to compare sizes, hopelessly unaware that his cock would never size up to that of Colin’s monster. 

Max, with shaking fingers, started to peel down Colin’s shorts once his little cock was fully erect, forming a nice tent in his underwear. To his surprise the nineteen-year-old didn't seem to be wearing any underwear, allowing him to easily just slide the shorts down his toned hairy legs. Max kept his eyes closed so as to not ruin his little prize: Colin’s fully revealed cock. His hand had brushed against its length, and from what Max could tell the member felt big. 

However he was taken aback when his eyes finally opened.

Colin’s cock was soft yet still managed to look bigger than his four-and-a-half inch length.

The thick soft dick rest against Colin’s right leg, surrounded by a trimmed patch of blond pubic hairs that lead up into that treasure trail. His large balls were a little hairier and hung low, looking like fun to play with. Even while flaccid, Colin looked like he was twice as thick as Max, who held his little member over it to judge for himself. 

Crestfallen that he was smaller, Max released himself to focus on Colin’s cock. 

Wrapping a hand around its shaft and giving a little squeeze, the boy whispered. “Oh wow…! He’s so big!”

Colin stirred a little, shifting around in his sleep. 

Much to Max’s delight, the nineteen-year-old turned towards him for better access to his sexy body. He was able to pull Colin’s shirt up further and see the older boy’s bare chest entirely. Slim pecs and two little pink nipples made Max moan quietly and reach out to touch them. The first ever time he had touched muscles, his slim fingers massaging down Colin’s body slowly. Running over the six-pack slowly, feeling the fuzzy blond hairs as he teased the sexy muscles chiselled into Colin’s chest.

Soon he was back at Colin’s treasure trail and followed it down.

“Woah,” Max breathed, playing with the softened cock. It fit perfectly in his hand, and with each stroke along the girthy shaft he could feel it start to swell. Going from about four inches to slowly ride up inch by inch. 

Colin’s moans were soft as the young boy played with his cock, blissfully unaware of it. His broad chest rose and fell a little faster as blood pumped down to grant an erection. Hardening in Max’s hand, the flared mushroom head peeling out of his foreskin the closer he was to hardness. In a matter of seconds Colin’s cock reached it magnificent peak: A thick seven and a half inch cock now rest in Max Reynold’s hand, too big for his little fingers to fit around. 

Max could only stare at the cock, which was close to double his length. He took a deep gulp of air, then gave the big piece of meat a few strokes.

It felt like trying to jerk off a flagpole, taking long and slow movements so he could feel its entire length. His hand brushed against the trimmed patch of hair surrounding the cock, then wrapped around the tip. All the while, Max squeezed lightly to feel its heat and pleasure the older boy without waking him up.

Watching curiously as the foreskin folded over Colin’s flared head, the young boy looked down at his own circumcised cock. Its little pink tip twitched excitedly as Colin released a louder moan. Pulling the foreskin back down as Max lowered down, the boy’s hand left the girthy shaft to instead fondle the heavy sack covered in blond hair so thick they made a small jungle. Massaging the squishing the orbs, Max felt the softness of Colin’s sack yet his firm cum-filled balls throbbing.

“Is mine going to get like that? Riccoli said he’s got a huge one too, but… oh man!” 

Max looked down and noticed something new about his play toy. From the slit, something thick and gooey was oozing out and starting to trickle down the front of Colin’s meaty shaft. The drop of whatever-it-is dribbled down and a curious Max was quick to scoop it up to get a closer look on his finger. It didn’t smell like pee, so what could be the harm.

Extending his tongue, the thirteen-year-old licked up the clear liquid. At first he recoiled at the strange taste, but as it lingered on his tongue the sweetness flooded his mouth and Max couldn’t help but moan. 

“Damn, guys make this stuff!? Mine never did that,”

Using one hand to pump his cock and the other to stroke Colin’s in an effort to make more, Max released a low moan. When his dick made nothing, the boy swapped to using both hands on the thickness of Colin’s cock. Pumping up and down slowly with a nice, tight grip he was rewarded with another few drops of the sweetness. So an idea came to mind that Max acted upon without even thinking. He leaned down low, supporting himself on one arm as he engulfed the monstrous head of his babysitter’s dick.

“Mm, that’s it Maxxy…”

Hollowing his cheeks, Max sucked on its tip for a while without moving up or down. Instead his hands did the work, stroking the base of Colin’s cock. Holding tightly around the base, Colin’s length throbbed with pleasure feeling Max jerking it off like an eager, hungry boy.

“Mmm…” The boy moaned, tasting every thick drop of pre that dripped onto his tongue. Lapping it up, his tongue flicked across the piss-slit so he could get a good mouthful of its sweetness which Max happily swallowed. Swirling around his tongue, Max stimulated Colin to the point where an eye peeked open.

At first Colin jumped in surprise, just a small jolt that bucked a half inch into Max’s mouth, shocked at what the boy was doing and moments from stopping him. However, as pleasure sunk into the nineteen-year-old’s body he allowed himself to relax into the couch and just see where this went; Max looked like he was loving the taste, and his small hands worked so passionately that Colin couldn’t bring himself to pry them off. 

‘Holy crap, this kid’s milking my dick! Mmm, if he keeps that up I'll cum on the double!’ Colin bit back a moan, struggling to act asleep. Even his girlfriend wasn’t this into his dick.

Max didn’t really know what he was doing so kept up his slow pace, his slim fingers wrapped tight. Pumping up and down he felt the cock grow slick after his jaw started arching. Some saliva escaped, pouring down Colin’s cock. But when he started to stroke it like that, the way it made Colin moan in his sleep took Max off guard. 

Wanting to try something new, the young boy knelt back down to swallow more than just the head this time. Max slowly moved up and down taking his time to get use to the odd taste of dick, using his wet mouth and tongue to pleasure the older boy. 

All the while his hands were lightly exploring Colin once more. He was nervous to touch, but those sexy washboard abs were irresistible so Max ran his fingers along the cracks or massaged the muscles as he moaned loudly around Colin’s thick cock filling his small mouth. He could feel it as the nineteen-year-old’s chest rose and fell in quick succession, the hitching of his breath while exploring every inch he could reach. At one point, Max’s dark brown eyes looked up at the face his babysitter was making and blushes. He looked so hot with his handsome face scrunching up in pleasure, a small smirk crossing his lips.

Colin wanted so badly to just shove his cock deep into the little throat sucking him, hating how long this was taking. Only about an inch or two were in his mouth, denying the full seven and a half inch cock the loving it deserved. 

‘Ugh come on little dude just suck it already!’ Groaning and trying not to thrust his hips, Colin fingers gripped a blanket laid across the couch.

Annoyed with Max’s lack of skill and slow motions, Colin’s hand took on a mind of its own by taking a gentle grip on the back of Max’s head and forcing the younger boy to move down on his thick seven and a half inch length. As expected there was a struggle as Max realised he was awake and the mushroom head started to slide down his throat. Forcing the walls open wider to accommodate its girth, causing Max to gag and struggle. 

“G-ghk!” He pushed on Colin’s legs to no avail. Just one hand was stronger than his whole body. “Mphhhhhh!”

Three inches, four inches, five inches filled Max’s virgin throat in a matter of moments before he really started to gag. Despite the struggle Colin held him down for a moment longer, eager to feel his whole cock buried in a boy’s throat just like that. But he couldn’t fit the other two and a half, so using a tuft of Max’s hair pulled the young boy off his cock. Quickly, Colin hooked a thumb around the base to keep his dick pointing upwards at the boy’s mouth, which hung open in a wide O-shape as his jaw ached. Colin was even thicker than he looked.

Grinning broadly with that same cocky, casual expression of his, Colin kept a tight grip on Max’s hair. Exploring the young boy’s chocolate brown eyes; Full of lust, shock, hunger and a hint of fear. All of which was so cute and just what he expected of Max. 

Max struggled to say anything with his jaw aching badly and that look on his babysitter’s face making him just want to stay silent. Something told him he wasn’t in any trouble, even after sucking another boy’s dick in his sleep. A phrase that sounded so strange and taboo that it was shocking to think he had just done that and the cock that was deep down his throat was just inches below, throbbing as if to say hello.

“You having fun there, kid?”

As Max almost jumped through the ceiling in fear, Colin’s voice was calm yet husky. “You’ve got some, uh…”

Colin wiped a thumb over Max’s lips, scooping up a drop of his precum. Licking it up happily, the dirty-blond loved the look it gained when he swallowed his own sweetness.

Gulping, the younger boy’s lips quivered. Nothing quite seemed real at that moment so his body went into auto-pilot. The hand returned to his hair, resuming its grip but he showed no reaction. Even as very slowly he was being guided back down, Max was too shocked by Colin’s actions to resist anything so followed down towards Colin’s dick. On instinct his lips wrapped back around the flared head, humming around the thickness for pleasure to the older boy without even knowing it. His small tongue slid against the underside of Colin’s cock, making it nice and slick as he was guided gently down a few inches before being pulled back up; All the while never coming to his senses being hypnotised by the taste of an older boy’s dick.

Moaning softly as the throat wrapped around his length, Colin thrust his hips up to meet Max’s mouth. Though the boy struggled and gagged slightly, he took five inches down his throat. Bulging slightly in his throat, the young boy felt it sliding deeper inside of him. Air blocked, he breathed through his nose but even that was a struggle feeling something so long easing its way down inside. Max groaned, pushing once more. 

This time Colin let him off.

“Your throat is hella tight, Max! Even my girl ain’t that good,” 

She was better, but he had to give the kid some compliments.

Sighing, Colin relaxed into the couch. His cock glistened with spit, which he started rubbing into the meaty shaft. “Like the taste or somethin’?”

“W-Well…”


End file.
